N,N'(Cyano-phenylene)dioxamic acids and esters

Abstract

It has now been discovered that novel compounds of FIG. 1 ##SPC1## are useful in the prophylactic treatment of sensitized humans and animals for allergy and all anaphylactic reactions of a reagin or non-reagin mediated nature. Additionally, these compounds are intermediates to the acids and physiologically acceptable salts which also have the same biological utility. The compounds of the invention are formulated with pharmaceutical carriers for oral, parenteral, inhalation or rectal means of administration.

We claim: 
     
       1. A compound of the formula ##SPC3## wherein W, X and Y are the same or different and are selected from the group consisting of hydrogen, alkyl from one to six carbon atoms, inclusive, phenyl, alkoxy with the alkyl group having from one to six carbon atoms, inclusive, hydroxy, nitro, halogen, trifluoromethyl and ##EQU1##wherein Q is selected from ##EQU2##and ##EQU3##wherein D is selected from the group consisting of hydrogen, alkyl from one to six carbon atoms, inclusive, phenyl, ##EQU4##and a physiologically acceptable metal or amine cation, m is 2 or 3. R 3  and R 4  are the same or different and are selected from the group consisting of hydrogen, alkyl from one to three carbon atoms, inclusive,   R 1  and R 2  are the same or different and are selected from the group consisting of hydrogen, a physiologically acceptable metal or amine cation, alkyl of seven to twelve carbon atoms, inclusive, and cycloalkyl of four to eight carbon atoms, inclusive, with the proviso that when one of R 1  and R 2  is hydrogen or a physiologically acceptable metal or amine cation, the other variable is not hydrogen or a physiologically acceptable metal or amine cation.   
     
     
       2. A compound in accordance with claim 1 wherein W is hydrogen. 
     
     
       3. A compound in accordance with claim 2 wherein W and Y are hydrogen. 
     
     
       4. A compound in accordance with claim 3 wherein W, X and Y are hydrogen. 
     
     
       5. A compound in accordance with claim 2 wherein X and Y are the same or different and are selected from the group consisting of hydrogen, alkyl from one to six carbon atoms, inclusive, phenyl, alkoxy with the alkyl group having from one to six carbon atoms, inclusive, hydroxy, nitro, halogen, trifluoromethyl, and ##STR33##with the proviso that when D is alkyl, the upper carbon atom limitation is three. 
     
     
       6. A compound in accordance with claim 5 wherein W and X are hydrogen. 
     
     
       7. A compound in accordance with claim 6 wherein Y is selected from the group consisting of hydrogen, alkyl of one to four carbon atoms, inclusive, phenyl, nitro, fluoro, chloro, trifluoromethyl and ##STR34##R 1  and R 2  are the same or different and are selected from the group consisting of cycloalkyl of four to seven carbon atoms, inclusive. 
     
     
       8. A compound in accordance with claim 7 wherein Y is hydrogen. 
     
     
       9. A compound in accordance with claim 7 wherein Y is at the 2 position and is the same as in claim 7 with the proviso that ##STR35##is limited to ##STR36##and R 1  and R 2  are the same or different and are cycloalkyl of five or six carbon atoms. 
     
     
       10. A compound in accordance with claim 9 wherein Y is hydrogen. 
     
     
       11. A compound in accordance with claim 1 wherein R 1  is the same as R 2  and neither R 1  nor R 2  is hydrogen or a physiologically acceptable metal or amine cation. 
     
     
       12. A compound in accordance with claim 5 wherein R 1  is the same as R 2  and neither R 1  nor R 2  is hydrogen or a physiologically acceptable metal or amine cation. 
     
     
       13. A compound in accordance with claim 7 wherein R 1  is the same as R 2  and neither R 1  nor R 2  is hydrogen or a physiologically acceptable metal or amine cation. 
     
     
       14. A compound in accordance with claim 9 wherein R 1  is the same as R 2  and neither R 1  nor R 2  is hydrogen or a physiologically acceptable metal or amine cation. 
     
     
       15. A compound in accordance with claim 3 wherein X is hydrogen. 
     
     
       16. A compound in accordance with claim 3 wherein X is 2-chloro. 
     
     
       17. A compound in accordance with claim 3 wherein X is 4-chloro.